Methyl iodide → HCID 44192802, compound

Participants

Reaction Conditions

Reaction Steps

At 0° C., NaH (2 eq) was added to a solution of 1 eq of compound 1-7c in DMF. After 30 min, a solution of 0.1 M methyl iodide in DMF was added slowly over 30 min, and then the reaction mixture was allowed to warm to 25° C. and stirred at that temperature for 1 h. After standard workup, the brown oil residue was purified by column chromatography, eluting with CH2Cl2/2% NH4OH. A brown oil (1-8c) was obtained in 84% yield. 1H NMR (CDCl3-d, 300 MHz) δ (ppm) 2.13 (s, 6H), 2.50-2.56 (m, 2H), 2.95-3.01 (m, 2H), 3.89 (d, 3H, J=1.9), 5.13 (s, 2H), 6.29 (dd, 1H, J=8.5, 2.8), 6.67 (dd, 1H, J=8.5, 12.1), 6.69 (s, 1H), 7.29-7.40 (m, 3H), 7.45-7.48 (m, 2H). APCI [M+1]: 327.2.

Provenance & Evidence